Dean, Jess, or Logan: The Real Debate

When Gilmore Girls premiered in October 2000, no one could've foreseen the impact a simple question like "which team are you" would have on generations. A lot can be said about someone based on which boyfriend they root for. Serious judgement may be passed depending on who you reveal your team to. There are two ways of thinking: either which boy is best for Rory or which boy is your personal favorite. It's time we discuss such important matters as these.

Rory Gilmore is a small-town girl turning sixteen who hasn't so much as held a boy's hand when we meet her at the start of season one. That is until the new kid in town takes a liking to her. Enter Dean Forester, boyfriend #1. Rory's intrigued by him; he's brand new in a town where everyone knows everyone, and also he's tall as hell. You can't blame a girl for taking an interest. Dean just moved to Stars Hollow from Chicago, and we learn he owns a motorcycle, enjoys fixing cars, and is a reader (however, this trait seemingly disappears from his character quite quickly). He ends up being Rory's first boyfriend, first kiss, and unfortunately in season four, first time. Dean is the boyfriend that is in Rory's life the longest. Their relationship starts innocently as any adolescent relationship might but over time turns tumultuous with lots of on-again, off-again toxicity. Dean is also widely known as the least favorite of all of Rory's boyfriends. He's co-dependent, possessive, hot-tempered, clingy, and selfish. During episode sixteen of season one, Dean tells Rory he loves her for the first time while on a date for their three-year anniversary. Rory doesn't know how to respond and, after a long pause, simply says, "Thank you." Dean proceeds to throw a fit over this and leaves Rory alone before ultimately breaking up with her for it. This is just the first of many infractions with Dean. He really only gets worse as the seasons go on, which is even more concerning because you'd hope he would get better as he matured and hormones subsided, but no. Now, to play devil's advocate, if I were to give props to Dean, it would be that he does care for Rory and wants to protect her. During the Chilton school dance in season one, Dean stands up for and defends Rory when Tristan Dugray starts taunting her. Okay, now that I've given him some positives, I need to go back to hating him, and I know the perfect way how. Dean gets married during season four and ends up cheating on his new wife with Rory; it's a huge mess, and Dean acts like a total jerk to his wife. It may be Jared Padalecki playing him, but nothing could give Dean enough redemption for me to like him.

Then you have Jess Mariano, boyfriend #2, Luke's troubled nephew who begrudgingly comes to live in Stars Hollow during season two. It's immediately portrayed during Jess' arrival that he is a rebellious teen and against the happy-go-lucky nature that is Stars Hollow. He does, however, take a liking to Rory upon meeting her. Jess is the fan favorite of Rory's boyfriends. Though it isn't apparent on the surface, the pair have a lot in common and get along really well. Rory's relationship with Jess is the most short-lived of the three boys but the one that probably leaves Rory the most impacted. When Jess leaves Stars Hollow at the end of season three, he essentially ghosts Rory. He simply leaves without planning to say goodbye and says very little when he does accidentally run into her. Jess had a much rougher upbringing compared to the other boys and isn't good at working through those struggles. This leads to bad communication and recklessness. Now to his credit, Luke really helps Jess in more ways than one and helps to give him the resources he previously never had. In a particularly bad moment, Jess forces himself onto Rory when making out at a party. The two hadn't had sex before, and Rory was definitely not wanting to do it right then and there. At first he doesn't respond to her pushing him off, but eventually she does get him to cut it out, and he immediately feels bad for it. There's also the general lack of commitment Jess shows to Rory over the course of their relationship, occasionally playing with her feelings and leaving the status of his commitment to be desired. Even though he has his reckless and sometimes arrogant or rude moments, Jess is regarded by many fans as Rory's "Luke" or her true match, in other words. This particularly works due to the literal blood relation to Luke that Jess has as well as the two being similar in certain lights. Though the pair never get back together post-season three, Jess does reappear sporadically over the remainder of the series. When he does return, he's quite different from the teenage version of Jess Rory dated. He makes something of himself and becomes the person Rory always believed he could be. This is what also wakes Rory up during her Yale hiatus in season six when she sees the life he's made for himself as well as him questioning her life choices. This prompts the iconic "why did you drop out of Yale?" line that Team Jess girls ride for. He's also an avid reader and writes notes in the margins, so brownie points for that!

When Rory begins her second year at Yale during season five, she meets Logan Huntzberger, boyfriend #3. Logan is really the antithesis of both Dean and Jess; he's rich, arrogant, sure of himself, and also blonde. He may also be the boyfriend that challenges who Rory is as a person the most. Part of this has to do with the fact that Rory is becoming an adult while she's with Logan, and thus, everything she knows about the world starts to change. She's no longer a kid growing up in a small town where everything she knows and thinks has come from her mother. For the first time, just as we all do, she's experiencing the real world without the protection of what's familiar. Logan gets a lot of slack for being the main reason Rory's character "goes downhill," but I wouldn't equate that all with him but more so her own struggles as a girl in her early twenties. It was bound to happen that Rory was going to fumble and make mistakes; she isn't the perfect daughter Lorelai believes her to be (it wouldn't be realistic anyway). When Rory quits Yale in season six and navigates inner turmoil, Logan is by her side through all of it. Allowing her to process things and go at her own pace but always supporting her. Jess and Logan were both very supportive of Rory; it was just that Jess had too much going on with him to always show it well. Richard and Emily Gilmore easily approve of Logan compared to the other boyfriends, as they know him and his family well; one might say "he comes from good breeding." However, the Huntzberger clan only causes more havoc and leaves the Gilmores with a bad taste in their mouths during season six. Thankfully, Logan is quite different from his family, even if Lorelai doesn't always want to believe that. Logan is Rory's most serious relationship, as they have been in a committed relationship (with only a couple rocky moments) for the better part of three years. They live together, they plan their futures together, and they are very involved in each other's lives (family, friends, work, etc.). This all accumulates to the end of the series, when on her graduation day, Logan asks Rory to marry him. Spoiler alert: she says no. When Taylor Swift wrote "Champagne Problems," she must've been watching Logan x Rory edits because it's truly so fitting. For those who don't like Logan, they would probably refer to him during season five. When we meet Logan, he's self-absorbed and arrogant; his main issue is when he lets his rich playboy ways get in the way. At first, he tells Rory that he doesn't do relationships but ultimately succumbs to Rory and decides to try a relationship, making Rory his first real girlfriend. His other major strike is when he and Rory are "on a break" (you'd think they'd know better after Ross and Rachel) when Logan believes they are broken up but Rory believes they are just on a pause; Logan drowns his sorrows by hooking up with one of his sister's friends. Rory ultimately forgives him but takes a while to get back to trusting him, so she freezes him out for a while. But they always come back together and demonstrate how much they care for one another; you don't just jump off scaffolding with someone and have it mean nothing.

The one thing all of Rory's boyfriends have in common besides Rory herself is being disliked by Lorelai Gilmore. I love Lorelai, but she absolutely gets on my nerves when she gets going on the boyfriends. Dean is ultimately the only boyfriend that Lorelai ends up actually liking, which is severely alarming. At first, Lorelai is apprehensive of Dean because he's Rory's first crush and interest in a boy romantically. She doesn't trust his intentions but ends up coming around to him and would prefer Rory with Dean over Jess. For different reasons, both Jess and Logan are bad influences and drag Rory down, according to her. When it comes to Jess, Lorelai is skeptical of him because she's unfamiliar with that kind of guy herself and never saw Rory with the brooding type. She doesn't trust him; she can't see him being a real fit for Rory. Whereas with Logan, she is far too familiar with guys like him. Upon hearing he's rich and in her parents' circle, she immediately dislikes him. Logan represents Christopher to Lorelai, and that is dangerous territory that she doesn't want Rory falling into. She quite unfairly pins everything that Rory does wrong on Logan when in reality he really doesn't have anything to do with the decisions Rory makes. Both Jess and Logan are much better fits over Dean for Rory for different reasons. They are also both a little too good for Rory and are saints for even putting up with her at times.

My vote? Well, I thought you'd never ask! Drumroll, please... I have always been team Logan. Logan represents one of the very few men I have ever liked who is blonde (IYKYK). With that said, I think Logan and Rory have the best relationship out of them all. They have their bumps, but for the most part they fit together really well and have a sort of domestic relationship that you can see lasting. When Rory refuses Logan's proposal, it's actually the most irritating thing for me to watch. They could've done a long engagement; they could've done long distance, or Rory could've moved with Logan to California, like suggested, and found a job there. Their being over just like that kills me, and I have to pretend it never happened. Now, do I necessarily agree with the all-or-nothing ultimatum he presented to her? Definitely not. However, I can see where he's coming from and why he did it that way, but I think they still could've found a way to be together no matter what their future looked like... but whatever. We all know the writing for the last couple seasons of the show (especially season seven) was a bit of a hot mess, so I'll just chalk it up to that. Even though I love Logan, I will admit to liking Jess and understanding the draw he has and why so many people love him and Rory together. As I previously stated, I do think both Jess and Logan are too good for Rory (and I'm not even that big of a Rory hater like so many people). As she gets older, Rory becomes far too stubborn, whiny, and dependent. I unfortunately could see her potentially dragging both of these men down over time if they were to be together. I think some of the dislike Logan receives primarily has to do with the fact that Rory really starts to dip as a character while he's around and the fact that people love Jess so much they only want to view him. When referring to teen Jess, I do not think he's a good match for Rory, but when referring to adult Jess, I can see the picture. I'm not sure which of the two is actually better for Rory; all I can say is that I love Logan. If Rory doesn't want him, he can come give me a Birkin bag, and I'd be more than receptive to his wooing.

Before we round this off, I wanted to give you a fun piece of trivia! While Rory is at Chilton, she has an interesting dynamic with fellow classmate Tristan Dugray. He is portrayed by heartthrob Chad Michael Murray. Tristan and Rory never date, but they do share a kiss. Tristan shows his interest in Rory in a, let's say, immature way, and Rory never reciprocates. In the end, Tristan ends up leaving school during season two. The reason for this is not my fun fact but rather commonly known. Chad departed the show in order to join two other WB shows, Dawson's Creek and then One Tree Hill (two of my favorite series!). There's also a fun nod when Tristan leaves, saying he's going to boarding school in North Carolina. Both Dawson's and OTH were filmed in Wilmington, NC. Fans as well as creator Amy Sherman-Palladino have discussed that Tristan's original arc may have included an on-again, off-again relationship with Rory. He was prompted to be the Logan before there was a Logan. He was rich, connected to the Gilmore circle, and also blonde. I think it would've been really interesting to have seen this play out and how Tristan's character would've evolved. He was far too immature to have been Rory's boyfriend in high school, but if he grew up a bit, it could've been an interesting storyline to see come back when she was at Yale. Instead, this relationship was brought to life through Logan, and I can't be mad at that outcome. Also, CMM needed to be Charlie on Dawson's and Lucas on OTH, so I'd say it all worked out for the best!

So whether you swoon over a Doose's Market aisle kiss, notes written in the margins of your favorite book, or shouting "In Omnia Paratus" in a ball gown, your love of Gilmore Girls is always heard. Whoever you choose, a lot can be said for the dedication we possess as GG fans. Debates like these keep our pop culture hearts thriving, so keep it up and remember to refrain from ripping someone's hair out when having your heated discussions!

Which team are you?

• 0%Dean 🏍️
• 0%Jess 📖
• 0%Logan ☂️